It is known to produce certain unsymetrically substituted 1,2-ethanediamines. Current processes, however, have proven unacceptable. For example, G. I. Braz et al. disclosed that the aminoethylation of aniline with ethyleneimine afforded only a 13 percent yield of N-phenyl-1,2-ethanediamine. The remaining product comprised polyamino ethyl compounds of high molecular weight. Dokl. Akad. Nauk., 59, 489 (1948), Chem. Abstr., 42, 6747 (1948).
More recently it has been reported that aromatic amine hydrochlorides may be reacted with ethyleneimine to produce the corresponding aromatic aminoethylated adducts, Ger. Offen. No. 2,057,744 (1972). Ethyleneimine, however, is considered very toxic. It would be desirable to provide an improved process for producing aromatic 1,2-ethanediamines. It would be further desirable to provide a process for producing aromatic 1,2-ethanediamine compounds that does not require highly toxic and dangerous reactants.
The 1,2-ethanediamines formed by the present process are an important class of materials which are useful as intermediates for the production of pharmaceuticals, photographic chemicals and other useful compositions. For example, N-(2-(methylphenylamino)ethyl)methanesulfonamide, is a commercially available chemical for use in photographic applications.